Shemale Threesome Stories

702 results
Orientation
Length
Category
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Infinite Scroll

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

Pam's Threesome Experience

by majicman21 on Apr 3, 2018
Loving Wives

Author's Note #1: This is a continuation of 'Pam's Shemale Experience' from the Transsexuals/Crossdressers category, as well as of 'Pam's Gangbang Experience' from the Group Sex category and 'Pam's Lesbian Experience' from the Lesbian Sex category. Reading those stories is hopefully not necessary to enjoy this one, although it will likely enhance said enjoym...

The Threesome Chronicles Ch. 04: Mary Evans

by SarabethW on Sep 12, 2017
Group Sex

Mary Meets Morgan Then, when all was jilled off and done, the tears would flow, and flow, and flow. Micah would eventually come to bed, quietly slipping between the sheets next to me, but never quite touching. He never heard my tears, and I would drift into sleep with my cheeks against my pillow, dampened by desperation and defeat. At times I would swear a...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Sally: His Perfect Shemale Partner Ch. 2

by PunkFan on Aug 31, 2017
Fetish

Thanks to everybody who e-mailed me, sent me a message on Yahoo messenger and voted for the 1st chapter. Being my first attempt at writing it made it worthwhile to know people enjoyed it. It has been a busy few months so writing this has being very difficult however next update/story will be much sooner. If you enjoy this chapter please vote for it and send...

Leather Shemale & Leather Wife

by LeatherKev on Sep 19, 2017
Fetish

I have always loved seeing others wear leather. I, too, love to wear leather and have a growing collection. I can't remember when it started but it seems I have always had this fetish for leather. During my first job out of college, I met a lovely young woman named Mikky. She was beautiful. Long dark hair, blue eyes, and long legs. All I could think of was s...

A Transforming Invention

by TransforMaster on Jun 1, 2016
Humor & Satire

In this story, somebody comes across a transformation device. This device allows the user to transform themselves or anybody else into anybody and everything. First choice is... What situation does this story start out with?What's next? Sara, a 24-year old student Sexy girl on a sofa! Two naked women(?) in bed Kate and Her Iffy Shapeshifting Chamber You are...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

My Girlfriend - A Shemale

by ARandomGuy on Apr 22, 2025

(hello everyone, who is reading this. so first thing, first. I'm not a first-time writer but my other account is gone. so this is my first story from this account. 2nd thing, I'm not the kind of guy who loves to jump on straight to fucking. so yeah, the story is gonna take some build-up but is not that long that you'll feel sleeping is better than this story...